


Heads or Tails

by levicel



Series: Heads or Tails - Tails, you win. [1]
Category: Supernatural
Genre: Alternate Timelines, Creampie, Cunnilingus, Dragons, Eventual Smut, F/M, Fluff and Smut, I dont know how this happened. I blacked out. Send help., Is it even a one shot anymore if I made a second chapter for one of the timelines?, Loss of Virginity, One Shot, Smut, There is ONE Sam chapter and the rest is all Dean, Vaginal Fingering, Virginity, asking for a friend, blowjob
Language: English
Status: Completed
Published: 2020-12-15
Updated: 2020-12-30
Packaged: 2021-03-10 16:47:09
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 16,528
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28080375
Author URL: https://archiveofourown.org/users/levicel/pseuds/levicel
Summary: You and the Winchester Brothers are hunting some dragons. When you find out dragons are hunting down virgins, well...  Your plans for the night change and quick!
Relationships: Dean Winchester/You, Sam Winchester/You
Series: Heads or Tails - Tails, you win. [1]
Series URL: https://archiveofourown.org/series/2086413
Comments: 63
Kudos: 104





	1. Coin Toss

“They’re  _ what  _ now?” you ask.

Sam sighs, not irritated by any perceived inattention on your part, but just… tired. You’d been hunting these dragons with the Winchesters ever since you linked up in Iowa. _“Three_ _heads are better than two,” you had quipped, “That’s how the saying goes, right?”_

Sam rubs his eyes -because, again, tired- and repeats, “The dragons are hunting down virgins.”

Yep. That was what you heard the first time. Your heart slams against your ribs while you force a neutral expression. “Interesting. Any idea on how?”

Sam shakes his head, fanning his arms over their “research”. The hodge podge piles of scrapped paper and open books offer him little comfort since he sighs again. Irritated. “Just…” He slides a book out from under a pile and points as if you can read it from where you’re standing. “They just  _ do _ . They can sense it from what I’ve got.”

“Like a V-card Radar,” Dean adds. Why he chose that particular moment to finally speak up when his mouth was half full with the greasy spoon burger he’d insisted on getting was anyone’s guess. You wish he’d kept his mouth shut.

“Yeah,” Sam begrudgingly agrees. “Except we have no idea how far it reaches. Maybe they need to be in close proximity? We could check out crowded areas. Look for suspicious characters. But maybe…”

“Maybe they can single them out. From anywhere,” you breathe. What if a dragon could find you here? This bunker was a fortress, sure, but dragons were mythical fucking beasts last time you checked. If this was rock-paper-scissors, you were pretty sure dragon beats bunker.

Burger gone, Dean smacks his lips. He must’ve touched a bit of ketchup because then he sucks his thumb clean before wiping his hands with a napkin. You watch numbly as he crumbles the napkin and tosses it in the empty to-go container. Good meal. Your stomach lurches. What if that’s what the dragons would look like? That napkin is your bones.

Sans food now, Dean strategizes with his brother. You try to nod along, hum at the appropriate intervals, but you can’t stop your mind from racing. Eventually, you snatch your jacket off the back of a chair and head out, “I’m getting some air.”

Dean is closer, so he cuts you off before Sam has a chance, but the younger Winchester is up on his feet too.

“Didn’t you hear what we just said?” Dean asks.

Oh, listening. Yeah, you’d been doing that. Totally. “I don’t care,” you deflect. “I’m going out for a drink.”

“A drink?” Sam’s voice is softer than his brother’s. That’s Sammy, always trying to understand. “If you want something, I’m sure we have booze here.” His lips curl up just a bit and he adds, “Dean’ll make you a drink.”

Dean’s head spins to his brother and then pivots back to you. Over the course of this hunt, you’d fallen into an easy pattern of teaming up with Sam to tease his older brother. It was never anything malicious and, hell, gotta pass the time some way, right? Dean is clearly still not a fan. If you hadn’t been sharing a smirk with Sam, you would have seen Dean go for your keys.

“Hey!” You jump up for them, but, with his height, he easily holds them out of reach.

“Ah, ah, ah…” Dean jingles your keys for emphasis. “You’ll get these back when you fess up.” He levels a stare at you. “What’s your game?”

Crap. You know that look. Just like when a dog catches a scent, they'll follow it to the end of line. Dean cages you in. End of the line. These goddamn Winchesters and their uncanny ability to sniff out exactly when someone’s hiding something. Even when that something is none of their goddamn business. You glare back at him, but Dean holds fast. 

You go over your options. You could threaten to take Baby just to piss him off, but then you definitely aren’t getting out. You could try to lie and cry about needing some time alone with your thoughts. They didn’t know about your past. Say it’s the anniversary of your dear ol’ Auntie Judy’s death or something. But nah. Any lie you came up with this fast, they’d pick apart just as quick. 

You look down, sighing in defeat, then you defiantly look right back at Dean. “I need to have sex,” you say bluntly.

Dean laughs once, mostly to himself. “It might feel that way sometimes. But you’ll be fine. Sammy and I will put headphones on and…” 

Sam is blushing, you think. You think because you can’t really look at him, but the bits you get from your peripheral say enough. All the while, you’re stuck in a staring contest with Dean. No blinking? Fine. You settle for a glare. Dean licks his lips, savoring how you squirm. Your glare can’t cover that. 

“...You can go to town,” he finishes.

You make a mad grab for the keys now behind Dean’s back. “That won’t work!” He moves the keys back up above his head. “Ugh! Just-!” He holds you back easily. The jerk is laughing at you. “I need to have sex tonight!”

Suddenly Dean gives up the fight. You feel your face heat up, knowing that they both know now.

“I need to have had sex  _ yesterday _ ,” you add, staring at the ground.

Sam, having closed the distance while you and Dean wrestled for your car keys, pipes up from behind his brother, “You’re a virgin?”

“How?!” Dean says incredulously. You and Sam both shoot him a look. “No, I mean, you’re-” Dean makes some kind of curvy hand signal and now your ears feel hot too.

“Can we not talk about it?!” You put your palm out. “Just give me my keys.”

“Wait, wait, wait!” Dean waggles his finger at you which is  _ STILL _ not him giving you your keys. “You were gonna just fuck some random dude at a bar?”

“ _ Dean _ ,” Sam interjects.

But you cut him off, “Yeah! That was the plan. Now-” You present your hand again. Dean is doing some kind of mental math that you have no time for. You flex your fingers, coaxing. “Time’s a-wastin’.”

Dean moves to hand your keys, but he keeps them hovering over your palm. “What were you gonna do?”

Your hand wavers because, wow, yeah. You hadn’t thought that far ahead. You shrug. “I unno. Ask a guy “Do you want to have sex?” or something like that.”

He drops the keys in your hand, but now you’ve lost your thunder.

“You don’t…,” Sam starts. You look up. He clears his throat and tries to laugh or smile, tries to shake off the awkwardness that's choking the room, but it's a shoddy front and you all know it. “You don’t have to go anywhere.”

Dean, for the second time tonight, looks to Sammy and then back at you. There’s a determined nod on his part as he agrees, “Yeah.”

You all three stand there. No one moves. The boys look uncomfortable as all get out and you can only imagine you look about the same.

“Well, don’t all volunteer at once!” you finally snap. You push past the both of them, ripping your coat off and throwing it just to throw something. “Jesus Christ!” You sigh and run both hands through your hair, leaving your arms up and your back to the both of them as you try to calm down.

You’re not even angry that they’re awkward. This is awkward. You’re not with them like that. You’ve only just met them and, sure, they’re nice guys and, sure, they’re attractive, but you’re not really into either of them like that. And now, what? One of ‘em is gonna punch your V-card? Both?! You think a stammering heart.

  
  


Dean breaks the silence. “Do we flip a coin?...” You hear Sam smack his brother on the back of the head. “Ow!”

“Who would you… Which…” Sam can’t find the right words and you don’t blame him.

You fall pitifully into a chair with a groan and cover your face with your hands so they can’t see you. You gesture blindly in their direction. “Can’t you just… flip the coin?”

You’re too preoccupied to notice Dean’s I-told-you-so look, but then you hear it, the distinct tinkling sound of a quarter spinning on a table, round and round, and then finally landing flat.

  
  
  



	2. Heads

**Summary for the Chapter:**

> Sam called heads.

Sam suggested going to  _ your _ room. You imagine he was trying to make you feel more comfortable, but you would’ve agreed to his too. His. Yours. Doesn’t matter as long as you… have sex. With Sam. Jesus, you are about to have sex with Sam.

You think maybe this could have been nice without the whole dire straits thing. Sam is sweet. You two got along well enough. Who knows? Maybe with time romance would have bloomed. Your stomach churns.

A knock at your door has you jumping out of your skin.

“Come in,” you say with a shaky voice.

Sam walks in, looking down bashfully as he closes the door. He locks it and you flinch again. He must’ve caught it because he gives you a little smile. He opens his mouth and you get the feeling he was gonna say “Relax” or “There’s no need to be nervous.”, but then he doesn’t and his hands flex at his sides like he’s not sure where to put them and he’s still at the door.

“So. How do we start?,” you ask, taking some initiative and closing some of the distance. The rest is up to him.

He gets closer and he licks his lips, slowly reaching behind your head. He’s never been this close to you before and he reaches for you as if expecting some force field to stop him. Or you to stop him, you think. Every moment he takes, Sam hesitates and maybe some of it’s nerves, but that can’t be all of it. He watches your every breath and movement.

“We could start here,” he says  _ -whispers- _ and gently pulls you to him for a kiss.

Okay. Kissing. You know kissing. Kissing is good. You step closer, pressing into him in a simile of what you’ve done in the past. This feels nice and you chase the feeling, searching for more. You tug his shoulders, forcing him to hunch lower and meet you. Your hands trail down his shoulders to his arms. You press and press, tiptoeing up to get closer. 

You need… You need something. You bite his bottom lip and lick, trying to find some fire. Kissing Sam is nice, but it’s just that. Nice. Apart from you pulling him, he hasn’t moved. If anything he moved away as soon he could and you wonder how someone can simultaneously initiate a kiss AND not return it.

“Look…” You pull away, cheeks flushed, and bite your lip. “We don’t have to do the whole-” You roll your hands in the air in hopes that the gesture helps you find the word. “ _ -kissing _ thing if you’re not into it.”

Sam’s face scrunches in confusion. “I’m into it.”

You laugh and, for the first time tonight, you feel a bit of the tension slip away. You cross your arms and huff, but your I’m-offended act is broken by your smirk. “You could show a little more enthusiasm,” you tease.

Sam nods a couple times. “Okay,” he says, biting back his smile. 

He takes your wrist and tugs you forward. You gasp and her pulse immediately skyrockets when he leads your hand down. Then he presses your palm against his steadily hardening cock. Experimentally, you keep rubbing him through his pants and he hisses. The sound shoots heat straight to your core. You didn’t know where to start, but you know what you want to do next. 

You coil your fingers into his pants and tug him forward, walking backwards to your bed. Once you reach it, you swap positions, pushing him back until he sits on the bed. Sam doesn’t protest in the slightest. He lets you straddle him and unbutton his shirt, lets you kiss down his neck and bite down on his shoulder. That one does earn you a delicious groan, so you catalogue it for later.

Sam doesn’t speak. He’s all breathy sounds while you kiss down his chest and it’s only when you reach his pants, kissing just under his belly button, that he says anything at all. “Wait… You don’t have to…”

You smile wickedly up at him. You couldn’t remember that last time you’ve heard someone talk like this. “I like doing it,” you counter, unbuttoning his fly and pulling his jeans and boxers down. Your toes curl at how obediently he lifts his hips for you.

He’s bare from the waist down, his shirt unbuttoned and hanging off his shoulders. You lick your lips and watch his cock pulse.

Sam swallows. “You’ve done this before?”

“This?,” you purr, circling the base of him with your hand and starting a slow pace. He closes his eyes and his thighs tense. He must really want to thrust up into your hand. Another flash of heat runs through you. “Uh huh…”

“I don’t-” Sam cuts himself off with a hum as you go just a little bit faster. “I don’t want you to do anything, you don’t want to do.”

Such a sweet boy, you think hungrily. You need a taste. He gasps when you take his cock in your mouth, his hands grip the edge of the mattress hard. You too easily imagine his hands in your hair, tugging like that, and you moan on his cock.

Your name rushes out of his mouth with a breathy curse. Soon the room is filled only with the wet sound of you slurping up and down his cock with your own muffled sounds peppered in. 

Sam mutters praises and curses under his breath as you work him. “Feels so good… Fuck. I want to touch you,” he confesses and you moan again. “Hmm… wanna-” He hisses. “Wanna make you cum.”

You can feel your pussy throbbing. Some time ago you started rubbing yourself, aching for some stimulation. When you pause, taking your mouth off his cock to tease him, Sam grips your biceps and pulls you up until you’re straddling him.

You open your mouth to object, but he cuts you off with a searing kiss, his hand digging into your hair and  _ pulling _ . You whine into his mouth and grinds into you, his wet, bare cock pressing against you. You never hated your jeans more.

Without pulling his mouth away, you feel him tugging at your pants. You want them off  _ now _ , but his hand leaves your hair for your hip, pinning you in place while his other hand slips into your unzipped jeans and under your panties. You jolt up, bucking into his hand, feeling his fingers slip against you. He traces your slit with one finger, circling up and down, barely there.

He hums into your mouth, slipping one digit into your heat. You break away from him with a pant, so his lips move to your neck, his tongue darts out to lick up the side until his mouth is just under your ear and you’re forced to hear him. His breaths come out in heavy pants, heating your skin for a moment only to leave you with goosebumps a second later. 

Your body goes from shivering to overheating and you partially blame your shirt for still being on. You press on Sam’s shoulders and his mouth is gone as is his hand. His hips shift under you like he’s ready for you to stand up. Unceremoniously, you throw your shirt across the room. “That’s better,” you say breathily with a smile.

Sam laughs through his nose and shrugs his shirt the rest of the way off. His smile fades when you suddenly do stand up.

You shimmy your pants and underwear off before you resume your position. “I mean,  _ this _ is better.”

You want to sound confident, but now your every nerve is screaming about how close he is to you. You feel like your pussy is radiating heat and self-consciously worry that he can feel it. You’re sitting higher than you were before, keeping some distance, but his cock is right there. Sam’s hand goes back to your hair, but he’s gentle now as he pulls you closer and the change makes your stomach flip in anxiety.

“Shh…” He kisses your cheek while his other hand trails down your body. His fingertips ghost along your skin, running down your chest to your bra. Fuck! Your bra! You should have taken it off! You angle your arms back to rectify your mistake. Sam’s thumb brushes over your nipple while his mouth goes to your shoulder. “We’ll go slow,” he assures.

You bit your lip, shutting your eyes tight, your nails digging into his shoulders, while he kisses down and down your neck and shoulders, his hands exploring all you’ve uncovered for him. You buck against empty air until his hand reaches your dripping pussy. Ever so often, you can feel his cock against your thigh while he fucks you with his fingers.

You moan his name, pressing into his hand whenever he takes a second to rub your clit, but he keeps moving away from the sensitive bit, keeps pressing his fingers deeper and deeper into you. He curses into your shoulder and you shudder.

“Please,” you beg. “More.” You can’t hold back a whine when he removes his hand completely. “Sam…” You open your eyes with a pout to find him sucking his fingers clean. “Fuck.”

Sam smirks at you, placing a hand on either of your hips and pulling you down. You obey without thinking, dumbstruck from watching him lick your wetness off his fingers, so you’re surprised when you feel his cock rubbing against you. He lets you enjoy one slow grind before he’s suddenly jerking you away.

“I don’t have any condoms.” His eyes are wide with the realization.

You laugh, relieved. For some idiotic reason, you were ready for him to call the whole thing off. “It’s fine,” you breeze. “I’m on the pill.”

Sam lets out a breath of relief as well. “Okay.”

“Okay,” you repeat to tease him.

With a smirk, he traces a hand back up to your hair, one still firmly on your hip. “Okay…” he whispers before closing the distance again.

His cock slots against you and, after all the build up, you think you could cum like this. Would that count? The hand in your hair tugs and you forget the thought, gasping into Sam’s mouth. He licks past your teeth, thrusting up against you. Fuck… maybe you  _ will _ cum like this.

You roll your hips in rhythm with him, but one time you’re off beat and the head of his cock presses into you. You both jerk away with a gasp. Sam recovers quicker than you, holding your hips steady while he lines himself back up.

“Are you ready?” he asks.

How does he expect you to say words right now? How is he still saying words right now?! You just nod enthusiastically.

He smiles at you, the kind of smile that crinkles his eyes shut, and kisses you short and sweet before guiding you down.

You close your eyes, leaning forward until you’re cheek to cheek with him. Your breath stutters and you hear his do the same.

“Easy…” he warns shakily. 

This feels so good, but so  _ much _ . Too much. You keep bracing yourself for it to hurt. You always heard it would hurt. There’s a soft stinging pain, but mostly you just feel full. “So full…” you sigh when you take the last of him.

His hands dig into your hips and he groans. “You’re so fucking tight.”

You huff a tiny laugh which makes your insides flex which makes  _ him _ flex inside you. That is a new feeling. “Virgin,” you remind, sitting back to face him.

Sam lets his hands lazily drag down your thighs before going back to your hips and he shakes his head. “Not anymore.”

Not anymore. Huh. You never put much thought into losing your virginity, but after so many years of being a virgin, you figured  _ not _ being one would feel... different. You don’t ask how because you don’t have an answer. And it’s not like you were waiting for marriage or love to lose it, but you figured you’d be dating the guy.

Sam smiles up at you, hands on your hips, thumbs brushing up and down. He doesn’t move. You haven’t moved yet. And you’re willing to wager that Sam would let you sit like this until one of you got a cramp. With that thought, something squeezes your heart.

You sweep a hand through his hair, admiring him. “Not anymore.” You bite your lip. “But just to be sure…,” you add with a roll of your hips.

The sound his cock drags out of you is absolutely filthy. You’d be embarrassed if he didn’t sound just as lost. You try to keep up a rhythm and he lets you rock against him, but then you scratch down his arm and then he thrusts up into you.

“Fuck, yes!” you cry. “Please, Sam! Please!”

His hands grab at you, tugging you, pulling you, showing you how to take his cock best. All you can do is brace yourself against him, silencing your moan by biting his shoulder. He goes even harder then, pounding into you, groanin. You squeak when his thumb brushes against your clit.

“You’re getting so tight,” he pants. You whine and writhe in response. “I’m close.”

Close? Your pussy clenches and he hisses.

“Where… Where should I-?” He can’t speak with the pace he’s started, but he’s not slowing down either.

He’s close, you think again, watching his brow furrow and lips part. His thumb brushes your clit again and your insides spasm. “Where?” you repeat dumbly.

He nods, eyes closing. “Tell me-” He groans. “Fuck…”

You flush impossibly hotter, putting together what he means. “Don’t stop,” you beg. Or order. You’re not sure. “Don’t stop. Don’t stop.”

Sam starts to argue, “I can’t-”

“Yes, you can.” You wrap your arms around him, holding him as tight as you can. “Please. Please. Please. Please, Sam. Please. I want it. Oh, fuck… I need it. Please. Please…”

Just like that, “please” is the only word you can remember. You say it over and over again while he chases his release. God, he’s going to fill you up. You were a virgin and now you’ll be full of cum. You moan and Sam grips your hips with bruising force, thrusting into you deep. He spills into you and before he’s even pulled out you can feel it dripping out of you. 

You rub your clit, riding his cock just a little longer. Sam plays your breasts, tweaking your nipples between his fingers before taking one into his mouth. “That’s it,” he whispers. “That’s a good girl.”

And you cum. Hard. Cumming feels so different with something inside you. Everything feels more intense. Sam is kissing her cheek and jaw and neck, whispering something. Him with the words again. How does he know words?

Once your breathing evens out, he asks, “You okay over there?”

You nod against his neck and you feel him laugh. His arms wrap around you and that’s all the warning you get before he’s laying back and pulling you down with him. There is a sticky mess between you and when you fall to his side, you cringe at the sound. 

Sam frowns, “What is it?” He’d been reaching to pet your head and now his hand is frozen above you.

You shake your head and cuddle next to him. You want to clean up. You really should pee. You’ve heard things and you know you should pee. But this is nice. “Gross sound,” you explain dreamily. Sam chuckles and combs his fingers through your hair. You let your hand rest over his heart. This is really nice.

“Thank you,” you sigh into him.

He takes your hand and you let him play with your fingers. He turns them this way and that, measuring each digit against his own. He laughs again and you don’t think you’ve seen Sam so giddy. “You don’t have to thank me.”

You stretch out with a groan. As comfy as this is, you will have to get up eventually. If just to change the sheets. “Oh, is that not the protocol? I wouldn’t know.”

“So, how was your first time?” he asks, fiddling with your hand again. He looks pretty focused on it. You don’t know Sam well, but you know he’s hiding something. Maybe that Winchester gene has rubbed off on you.

“Great.” You kiss his shoulder with a loud, hammed up muah. “I really liked when you were all  _ rawr _ !” You flourish your statement with a playful bite. “You could do that  _ more _ .”

Sam laughs again. How many is that now? You’ve lost count. “I didn’t want to hurt you,” he defends.

You get up. You get up now because you’re worried if you don’t, you might stay there and fall asleep there and the mess on your thighs isn’t going anywhere. You bite your lip at that thought, but shake it away.

“Pssh! I get thrown around on the daily,” you counter. “I’m sure I could take whatever you got, Winchester.”

Sam sits up and says, “Is that so?...” 

Holy Hell. His gaze pins you place. Why are you out of the bed? You should be in the bed, your brain screams at you. Sam is in the bed and he’s giving you hungry eyes and-

“Hey! Hey!” Your voice wobbles as heat washes over you. “Down, boy. Give a girl a minute, huh?”

Sam’s eyes trace a line down your body. You shiver as if it’s his hands again drawing their way back down. When he reaches your thighs, glistening and sticky with your shared release, he licks his lips. “Yeah…” he agrees. “I think you had enough.”

You turn away from him completely and he’s laughing again. Do you like giddy Sam or hate giddy Sam? What’s the verdict on that? Or is the jury still out?

You head to the showers and Sam follows. That makes sense. He had a mess of his own to deal with, after all. But things feel normal and that doesn’t make sense. You thought tonight would change things, change you, change your relationship with Sam, just… things would change.

Later, you’re both dressed and going about your own business. Just a normal Tuesday. No awkward silences. No weird thing where you go to pass him in the hall, so you go left, but then he goes left, so you go right, then so does he, and you both go on like that forever and forever, ad infinitum. You still kind of ache though and each time makes you rub your thighs together. That definitely wasn’t the case last Tuesday.

You make dinner together normal. Check. You eat together with him and Dean normal. Check. Dean doesn’t mention it and, yeah, that’s not really a check, but- Check. Sam drops off some late night coffee before he takes his seat. Check. He’s not quite to you yet, but you know that’s what he’s doing. And just as you’re mentally tallying off another normal occurrence, when he bends down to hand it to you, he kisses the top of your head and your heart flutters.

  
  


**Notes for the Chapter:**

> I am pretty dang happy with how this came out. It's super easy to write a whole "they've been pining for each other this whole time" thing or "they fucked so now they're in love", but i wanted something that is more like a friends with benefits, heavy on the friend part. (It's okay to give your bro head sometimes, right? No one answer that.) I cannot resist me some floof and smoof, okay?! I'm weak! Hatesex? We don't know her. We like the people we fuck and we show it, bb.
> 
> The Dean chapter is nextttttttt!!! 
> 
> If anyone is reading this, please leave a comment. I love, love, love comments. They nourish my soul.
> 
> OH! I wanna clarify that Sam would eat the kitty, okay? He just didn't that night. We don't fuck around with these men who don't wanna eat! Okay, byeeeeeeeeeee!


	3. Tails

**Summary for the Chapter:**

> Dean called tails.

Dean insists you use his room. You don’t care where you two do it, but you couldn’t stand to be agreeable when he was all… all… You think back to him, looking you up and down, appraising you, planning. No, _scheming_. Had to be scheming. That look on his face while his eyes dragged down your body had been certified Bad News. Your body burned under his gaze and you loved every bit. Of course, you gave him shit for it. That was how things worked.

You honestly don’t know where the teasing began. The manic, “I’m not touching you”-esque pestering just screams little brother to you, so you put your money on Sam. But “He started it!” also sounds on brand and you second guess yourself. You feel the answer, festering under your skin, but you’re almost too stubborn to admit it. Which is absolutely bonkers considering you’re about to have sex with the guy.

Your stomach flips and you pause in the hall. Dean’s room is just a couple doors down. He’s in there. Waiting. And your body burns again.

He’s too pretty.

No one is there to see you, no one could even hear you, but the confession makes you bite your lip. You saw Dean and instantly thought he was hot. It was like a slap to the face how hot he was, but _then_ you saw his shit-eating grin and you thought “Oh no. He knows he’s hot.” And from then on, you took pleasure in knocking him down a few pegs. So if Sam set you up, you had to take it. No question.

You start walking again, fidgeting with your hands. Sam did it too!, you argue to no one. It’s just as bad as he started it.

The door whips open and you jump.

“Are you gonna come in?” Dean asks, irritated. He gestures up and down the hallway, adding, “Or you gonna pace out here some more?” Then he’s sighing and heading back in his room. “No problem. Take your time.”

His voice is too forced to be sincere. Is he calling you chicken?! You push past him. “I was not pacing,” you argue and too late you realize -if the grin is anything to go by- that you did exactly what he wanted.

He locks the door.

“Who’re you keeping out? Only other person here knows what we’re doing,” you point out. You’re going for snooty, but your voice wavers enough that you miss the mark. You clear your throat. “Think he’ll try to get in?”

“Old habits,” Dean shrugs, stalking over to you. 

_Walking_ , you correct. He’s just walking. This is his room and he can walk in it. You’re taking slow breaths through your nose when you notice Dean has closed the distance between you. You look up at him instinctually. He leans his face down to yours.

He’s going to kiss you. Alarms go off in your head. Dean Winchester is about to kiss you!

At the last second, you turn your head. “ I don’t want-” You bite your lip. If you say “I don’t want to kiss” out loud to one Dean Middle-Name-Unknown Winchester, he is going to know without a shadow of a doubt that you are lying. You’ll never be able to look at him or that insufferable grin again. “We don’t have to kiss.”

Dean hums in thought before saying, “Pretty woman. Alright.”

Deep inside, _deep_ and hidden, you preen because he said it like “Good idea!” Then you think it’ll be awkward and there will be some delay, but Dean just latches onto your neck and slips his hands WAY too easily under the back of the shirt. 

“You, uh…” Your voice comes out breathy already and you squeak as he finds a particular spot near your collarbone and you close your eyes. “You a big Julia Roberts fan?”

What?! Self, what are you doing?! What are you talking about?! Before you can berate yourself further, Dean responds with a hum. The sound buzzes across your skin and his breath comes out hot.

“I like that movie,” he whispers. Must have whispered. You could barely hear him and there’s nothing else that would be preoccupying your senses at the moment, so he must have been whispering. “When he puts her on the piano…”

Dean’s gone all the sudden. Your eyes shoot open while you pout and- Oh. No. He’s bent down. Then he wraps around the back of your thighs, pulling you close to him, holding you up in the air as he stands straight. You’re pressed impossibly close to him like this and clinging to him so you don’t fall. His hands grab a firm hold of your ass that you don’t think is just for balance. When you meet his eyes, he’s appraising you again.

“Yeah,” he drawls, shifting you so you meet properly. You both still have pants on, but more alarms are screaming that his cock is right there. You feel like your pussy is pulsing heat and your cheeks flush because you’re sure he can feel it through your clothes. “That was hot.”

He tries to angle you down to him, but with hands on your butt, he can’t pull you down himself. You keep your shoulders away, looking at the wall. Sensing your apprehension, he puts you down.

“I am going to have to touch you,” he reminds. As if you fucking forgot that part! He runs a hand through his hair. “Do you need me to turn the lights off or something?”

Maybe he’s trying to be sweet, but you’re so ready for condescending that you snap back, “No. I don’t need the lights off. I just need-” You cross your arms and turn away from him, but that shows you his bed, so you pivot to face the nightstand. Good Ol’ Unassuming Nightstand.

“You need to relax,” Dean finishes for you, hands on your shoulders. Then he’s spinning towards the bed and walking you forward until your legs hit the mattress. “Sit.”

You glower at him from over your shoulder.

Dean rolls his eyes and, with far too much ease, flips you around and shoves you back on the bed. You huff in offense as he unzips your pants. He pats your flank before he tugs and you ignore that you lift your hips.

“Good girl,” he says, unthinkingly, mostly under his breath, and the throwaway phrase sends a rush through you.

“What are you going to do?” you ask, sitting up on your elbows, and you already know the answer by the comfy position he’s taken between your legs. But you want to hear him say it. You want him to say filthy things to you with that stupid, pretty mouth.

“Shh…” He sits up tall and traces a line down your neck to your sternum. His palm spreads across your chest and he slowly pushes you back down. “You just relax.”

You look up at the ceiling, not daring to look at him, but you feel his mouth searing into your thighs, kissing a trail up, up, up. His lips drag along the hem of your panties and you gasp, every muscle tensing, but his lips continue on, ignoring your pussy and making it throb.

“Relax,” he teases.

You open your mouth to say something smart back, so you’re helpless to stop the sound when his fingers drag along your covered slit. He hums into your skin, fingers pressing a bit harder. You roll your hips, trying to get more friction, but then his other hand is holding your hip down, pinning you in place.

Fuck. You bite your lip and let your head roll against the bed. He’s strong. That is unfairly hot. 

His mouth is searing now as it works its way to his fingers. Since your panties are still on, he’s rubbing your own slick back onto you. The material is drenched in the center.

“Such a good girl,” he pants and, without thinking, your hands grip the bed sheets, clawing into the material. The way his hands still for a breath, you know he saw. 

The kiss he places on your hips makes you jump. “You like being my good girl?”

You wiggle under him, but bite your lip hard, turn your head into the bed, unwilling to admit defeat.

His next kiss is just under your belly button. “Hmm… look at you. All laid out for me.”

Your eyes are shut so tight that you have no warning.

His mouth is over your clothed pussy, licking and sucking. When you cry out, he moans against you, “So fucking good for me.”

Your hands dig into the sheets once more, knuckles white as he pulls your panties to the side and licks a stripe up your pussy. You roll your hips for more, but then his other hand is back to pinning you down and you whine. He only teases you like that for a couple more agonizing licks before your panties are removed, tossed and lost in his room.

When he resituates himself, he pulls your legs up on his shoulders. His mouth is all over you without your troublesome underwear getting in the way. You’re completely naked from the waist down and you suddenly feel off balance, unsymmetrical. You can also feel sweat building under your shirt. You shift up to take it off, but Dean’s hand slides up, _under_ your shirt, gliding across your skin, to push you back down again.

You mean to protest, but he must anticipate it because he sucks on your clit to distract you and all you can do is fall and grind against his face. His hand still under your shirt, gropes and massages your breast over your bra. You jut your chest into it, aching for more. 

“Dean,” you plead. You try to sit up again and now both of his hands force you down. “Dean…,” you moan appreciatively. You were going to say something. His tongue makes you forget words. You’re sweltering. “Dean, stop.”

He immediately leans back, lets you wiggle your legs off his shoulders and sit up. You rip your shirt and bra off and you might as well have been wearing a corset. You can _breathe_. Dean is also giving you a break and- Yeah, you think, your head fuzzy, you probably need to do that.

Dean licks his lip, tasting more of you. Fuck, his face is all wet. “You good?”

“I was hot,” you say, gulping down another breath.

“Still are from where I’m sitting.”

You scoff, blushing, ignoring his hands running up and down your thighs, “Does that line work for you?”

“I have a naked woman in my bed,” he counters with a shrug.

He does. You’re naked as the day you were born and he hasn’t taken a thing off. The imbalance turns you on when you think about it. _“Hmm… look at you. All laid out for me.”_

“I cannot stand you,” you laugh and shake your head. The lie comes out so easily. Dean doesn’t even look hurt. He obviously doesn’t take the things you do to heart. Still, he’s here with you now and you feel like you owe him a little honesty. “Sometimes,” you add.

You expect some smart ass remark, some gloating, _something_. Dean’s smile changes as he laughs through his nose. It’s smaller, but not any weaker. The other looks he gave you made your skin flush, but this tiny smile makes your heart flutter. This smile is quiet and cozy.

So you kiss him.

You mean it to be soft and sweet, a one and done kind of deal -like the deal you’re currently in- but when you pull away and lick your lips and taste yourself, you feel something wicked wake inside you. You let him pull you back in. From the manhandling earlier, you thought Dean would be rougher. You try to be. Your toes curl as his lips glide against yours, soft and coaxing, and you melt into him, only to feel your naked chest brush against his shirt. You let him undress you without getting a single thing off of him. Why did you do that?

_“You like being my good girl?”_ replays in your mind and you moan into him, clawing at his arms. Dean smiles against your lips, grabbing two handfuls of your ass and pulling you flush against him. You’re about to push him away and give him shit when he sucks your bottom lip, sweeping his tongue along it before he lets go. There goes yelling at him for teasing you about being into it. Actually… you take a second to enjoy all the sounds _he’s_ making, the soft pants beating against your skin, the low rumble of his groans while he kneads your ass.

Encouraged now, you start to unbutton his shirt. He breaks away and his hands rip away from you. He unbuttons enough to pull his shirt over his head. Oops, you think, as you hear tiny pieces of plastic hit the ground. He didn’t do enough buttons. You’re watching one button roll away and you scoot over to get it.

“Forget it,” Dean says followed by the sound of a belt buckle. 

Your head whips back to him. Yep. He is taking off his pants. The shirt is gone and he is taking off his pants. Alarms go off again.

“Hey,” Dean calls quietly to get your attention. He’s talking to you like you’re a scared little bunny and what’s worse is that you kind of feel like a scared bunny. “You okay?”

This does not have to be a big deal. Sure, things are going to change after this, you think and your stomach churns. But change isn’t always bad.

He's naked. You're naked. You are going to have sex. Each thought makes your anxiety grow which is dumb. You've liked everything so far. Dean is a great partner. You'll have fun, you tell yourself. But you kind of always figured you'd lose your virginity with someone you were dating, someone you liked. Well, you like Dean. Someone who liked you then.

Dean frowns, his mouth flaps open and closed a few times before he figures out what he wants to say. "It's okay to be nervous."

You know he's being sincere, but you can't help but laugh at him. He sounded like he’s in some cheesy After School Special and he just called for his line. You cut off your laugh as a courtesy. Before you lose your nerve, you ask, "Do you like me? ...Like, as a person?"

"Do I like you. As a person," Dean repeats flatly.

He's right. That was a dumb question. You're about to tell him to just forget it, but he scoots over to you and tugs you close to him. When he tilts his head down, you close your eyes. Then, you squeal as he flip you down, your back now flat on the mattress. His body is caging you in and now that you're under him, he pulls your legs up to rest on his hips.

"Of course," he says like you're an idiot for asking.

It wasn't even a second thought for him. I like you and the sky is blue. You glare at him even as your heart flutters and open your mouth to tell him he doesn't have to be a dick about it, but then he's kissing you to shut you up. Dammit, he is a great kisser. But you resign yourself to stay mad at him.

"Now stop overthinking things," he whispers and then kisses you on the cheek. Then down your jaw, your neck. You don't have a rebuttal and it's too hard to act like you don't like what he's doing. "Just be in the moment."

The moment. This moment? Where Dean is kissing up and down your neck and lining up his cock with your-

"Oh, fuck!" you gasp as his cock slides against you.

"Shh… I got you, babygirl," he pants against your neck.

"Dean," you call to get his attention, but you end it with a whine because he's still grinding his cock against your pussy and each thrust up brings him to your clit. Then he leans back on his knees and a helpless whine tears out of you. "Huh?... Why'd you stop?"

Dean's fingers are inside you, reaching a spot that makes you scream. "Gotta make sure you're ready."

He pistons his fingers into you, curling the digits and coaxing more noise out of you. Your eyes shut as you take his advice, living in the moment and enjoying him working you over. Somewhere along the way, you heard a drawer open and a wrapper, but Dean's fingers fucking you took precedent, especially with what he was saying.

"That's right. Such a good girl."

Your back arches off the bed.

"You gonna cum for me? Hmm, fuck. You feel like you want to."

You're a mess of moans and pants and is that you begging? All you can feel is his fingers on you and a delicious pressure building.

"Come on, baby. That's it. That's it."

After you cum, you have to grab his arms to stop him. You try to mutter "Too sensitive." but you end up too mumbly and you hear him chuckle.

When he settles back over you, you lazily wrap your arms around his shoulders, hugging him to you and pressing a kiss to the space between his neck and shoulder. Then, the head of his cock presses against your pussy. ...It feels different. You frown and look down. Oh. A condom.

"I'm on the pill…," you think aloud with a pout, unsure what you're trying to argue.

Dean squints at you and smiles. "I can take it off…?"

"No!" You violently shake your head before tucking your head in the crook of his neck, feeling like your face is on fire. "No. This is fine."

You pop your hips pop in a silent "Get a move on" and feel him shimmy his hips before his cock enters your pussy. You wrap your arms around him, squeezing him tighter.

"That's my girl… I got you." His gentle words are overtaken by a groan. "I got you."

Once he's seated inside you, he kisses up your neck, nudging your head to get you to look at him.

"How you holding up?" he smirks and it doesn't have the bite you’re used to since he's so breathless. Seeing him like this, so desperate for control and losing it so steadily, is exhilarating.

"Good," you say in your best how's-the-weather voice, but you sound wrecked. You’ve never felt so full. You messed around with your fingers before, but this is so much more. He flexes inside you and you have to close your eyes. "You?"

Dean licks his lips and nods, “I’m good.” 

Then, he rolls his hips, watching your face the entire time. Each pull out and each thrust in pulls a whine from you, each one, agonizingly slow. You hook your legs higher on his hips, wrapping your legs around him more firmly, pulling him closer, urging him to go faster and harder, but he doesn’t stop.

“You feel so good, babygirl,” he groans before kissing you.

Dean _never_ called you a pet name before tonight. That was a goddamn shame. You shivered thinking about him calling you that outside the bedroom. Now that you knew what his cock felt like, what his tongue felt like, all of him. You knew what _he_ felt like now and if he whispered “babygirl” into your ear out in public, it’d be a promise for more of this. 

He goes just a bit harder, hitting something inside you and you pull away from the kiss. “Fuck, Dean! Yes! More…”

“This what you need?” His hips smack into you. Jesus Christ, you can hear how wet you are. “Tell me what you need.”

“I…” You swallow, closing your eyes while you take his cock. “I want-” You moan, clawing into his back. “I want to make you cum.”

His head falls to your shoulder with a groan and you card your fingers through his hair with one hand. He did so much to make you feel good. You wanted to see him fall apart for you and fuck being shy about it when his cock is inside you.

“You feel so fucking good. Hmm…,” you moan, licking the shell of his ear. “I want- I want you to fill me with cum. Fuck… Pump all that cum into me.”

Apparently, creampies are an affinity you and Dean have in common. He moans into you, his hips slamming into you in a desperate rhythm. He braces himself back on his arms so he can fuck you deeper and harder. You lick your lips, watching his face contort in pleasure.

“And call me babygirl,” you order.

Dean smirks, instantly complying. “Fuck, babygirl… I’m gonna cover this pussy with cum. You’ll have… cum dripping… out of you,” he pants breathlessly.

“Yes, yes, yes…”

Dean hisses your name and groans, thrusting deep as he keeps his promise and cums. You rub your clit desperately and Dean gently kisses down your collarbones to your breasts, licking and sucking one nipple while his thumb works the other.

Dean hums into your skin, “You gonna cum again for me, babygirl? Hmm… that’s it.” For your benefit he grinds his hips into you slowly, kissing your neck, jaw, and cheek as you come down from the high, and, with a sigh, flops onto his back at her side.

Dean heaves another sigh and laughs,” Fuck…”

You catch him slipping off the condom and tying it off as you scoot onto your side. He’s leaning away, presumably to toss the used condom, so there’s some place between you. You’re not sure what happens now. You wait for him to lay back down to say anything.

“Thank you,” you say as you fiddle with the sheets.

“You are absolutely welcome.” Dean groans as he stretches. “If you need more help, call me _anytime_.”

You throw a pillow at him and bite back a smile. “I think I’m good.”

He shrugs and most frustratingly _uses_ the pillow you threw at him, tucking it behind his head. “The nights get lonely sometimes.”

You can’t help but giggle. “You’re ridiculous.”

“I’m right,” he counters. “Now come here.”

You allow him to pull you into his side. When you look up at him, his eyes are closed and he looks peaceful. A part of you doesn’t want to disturb him, but...

“We can’t go to sleep yet,” you argue.

“We’re just gonna lay here awhile. No rush to get back out there.” His one hand traces a line up and down your spine. His eyes are still closed. You open your mouth and the hand on your back is suddenly slapping your ass. “Shh.”

Eventually you both get dressed again and you part ways. After the sex and Dean’s offer of more sex, you thought being in the same room as him might be Innuendo City. You thought you would be awkward around him, but if anything you’re both more comfortable around each other and if you didn’t know better, you would have said nothing changed.

Except at dinner you ask Dean to pass you the salt and he says, “Sure thing, babygirl.” He doesn’t wink, doesn’t ham it up, and, again, if you didn’t know any better, you would think he always did that. The moment’s too fast or perhaps too mundane for Sam to notice, so you figure you misheard him and take the salt without another thought.

**Notes for the Chapter:**

> AHHH!!!! I am deceased! I had so much fun writing this. The parallel, alternate timeline thing was so fun as was planning out how each brother would act. SO MUCH FUN!
> 
> I think if I absolutely HAD to pick, I guess I'd pick Dean, but my heart also belongs to Sam, so I don't knooooowwwww. That's why I wrote this, y'all! I want it all, babyyyyy. I just love people being sassy with each other.
> 
> Also, reader exploring some kinks with Dean?! I don't know why but I think that shit is wholesome as fuck.
> 
> Thank you for reading this. Please comment. I love reading comments. :P


	4. The Tail End

**Summary for the Chapter:**

> Sequel to Ch. 3 a.k.a Dean's chapter
> 
> This is set after you hunt the dragon. SPOILER ALERT: More sex happens.
> 
> P.S. I edited a part to make the reader's motivations more clear. I don't know if it worked.

This bar is a dump, but, after the shit you all went through, it feels like an oasis. It’s probably because of adrenaline, but you’re feeling goofy and giddy. Being in a modern day tavern after killing a dragon helps lend to your silly mood.

“To slaying the dragons,” you say with your best British accent, raising your bottle. You look across the booth to Sam and then to Dean at your side.

“To slaying the dragons,” Sam says in a deep baritone and you think he was shooting for an accent as well. He lifts his bottle in the air.

“And to saving young maidens,” Dean adds, lifting his drink. Your eyes bug out of your head at how easily he took on the Knightly voice.

“Cheers!” You laugh and clink your drink against theirs before taking a sip. It tickled you to think of Dean as a knight in shining armor. But he was, wasn’t he? “Yeah… I wouldn’t have gotten to kill a dragon.” You turn to Dean. “But I did because we had sex!” 

You merrily cheers your bottle against Dean’s.

“How much has she had to drink?” Sam asks, pretending to whisper.

You chug the rest of your beer and slam in on the table. “Not enough. Sam, will you get me another one?”

Sam just laughs, “Why can’t you?”

You pout dramatically. “Because.... I’m stuck.” You feign pushing Dean out of the way. “See?”

Sam turns to his brother, but Dean’s lips just curl around his beer as he goes for a drink. “She’s stuck, Sammy.”

Sam shakes his head and gets up.

“Hey, uh-” Dean licks his lips, trying to sound casual and keep his smirk at bay. “While you’re up get me one too, will ya?”

Sam grumbles something and you giggle at his back, so you don’t notice that Dean has closed the little space between you two until it’s too late. You _are_ stuck now.

“Now why did you send him away?” Dean asks and you realize that his arm is wrapped around the back of the booth, around you, and that it has been this whole time. 

You fiddle with your empty bottle. “I… wanted… to thank you.”

“Oh.” Dean leans back into the booth, away from you. “Yeah, no problem.”

You bite your lip and glance around the bar. It’s busy for a small town place, but it’s late enough at night that everyone around is sloshed compared to you and the boys. No one notices your hand slipping under the booth to rest on Dean’s thigh. 

“I _want_ to _thank_ you,” you say slowly, rubbing and gripping the denim. You peek over to him to gauge his reaction and you swear if you have to spell it out any clearer you might die of embarrassment because- 

~~~~

“What the hell?,” Sam later says to an empty booth. 

~~~~

“Classy,” you remark as you file in and Dean locks the bathroom door. It’s a small single person set up. You mull over pretending to be grossed out or offended, but between his eagerness and the semi-exhibitionism, you’re too turned on to ever sound convincing, so you settle for the truth. “You know I didn’t mean right now, right?” 

“What?”

He sounds so genuinely and completely blindsided that you can’t help but laugh. “You’re adorable,” you say as you get up on your tiptoes to kiss him.

When he pushes you back against the door and starts kissing down your jaw, you realize that you’re in trouble. You push him by the shoulders to break him away and, with the extra space, you let your hands travel down his chest, your eyes following the same path appreciatively.

“Why'd you follow me in here then?” he asks gruffly.

“ _Follow_? You dragged me in here!” Wait. You’re fighting. Stop it. You shake your head and take a breath. You trail one hand up and fiddle with the hair at the nape of his neck. “I want to thank you properly. With a bed.”

He rolls his eyes. “I don’t need a bed.”

You scoff. You’re trying to be sexy, dammit! Can’t he respect that?! “Well, I’m not kneeling on this floor,” you argue. “And I want to suck your cock, so who’s sneaking into whose room tonight?”

There. Down to business. You wanted to make it a sexy thing, but, no, Dean had to ruin your plan. You peek up at him and your angry pout is met with a smoldering look. You don’t even think twice as he leans forward; you close your eyes, waiting for his lips against yours, waiting for him to grab your waist and pull you closer.

CLICK.

Dean unlocks the door and opens it. “Ladies first.”

You awkwardly shuffle sideways to get past him, glaring at him the whole time. He could move an inch, the jerk! You barely have the space to get by and you know for a fact that he has plenty of room behind him. Once your back is to him, you feel his lips at the nape of your neck, pressing to your flesh in a chaste kiss.

“Your room tonight, babygirl,” he purrs, then slaps your ass. “Get the lead out,” he says normally. “Sam’s probably wondering where we are.”

“That was fast. _Really_ fast,” Sam remarks as you and Dean shuffle into your side of the booth. Sam winces at you in sympathy. “I’m so sorry.”

“Hey!” Dean huffs in offense. He grabs the beer that’s been waiting for him. “Shut up.”

You try to smile normally, but you feel Dean’s hand trace the edge of your shoulder. “How long are we staying out tonight?” you ask casually.

You hear the tiniest chuckle from Dean and you hope your cheeks aren’t as pink as they feel.

“I don’t know,” Dean drawls. “I think we deserve a night out.” His gaze slides over to you. “What’s the rush?”

You chew your lip. Then clink his bottle with yours and “You’re right.” comes out a lot like “You’re on.”

~~~~

Dean was decidedly tame at the bar. Not that you expected him to be too overt with his brother around. Still, each lingering touch just made you buzz with excitement and you couldn’t wait until you got him alone. Dean drove you crazy and you wanted to give him a taste of his own medicine. It was just too easy to melt into him when he touched you. 

“Maybe I should tie him up…,” you think aloud. 

Would that be too much? You did your best to pull out all the stops this time. You didn’t have much in the realm of lingerie, so your cute, matching bra and panties would have to do. You had never bought thigh highs before because, first of all, you didn’t have anyone to enjoy them with and, second of all, thigh highs were not necessary for ANY hunt. You packed _essentials_ only. Only now, looking down at your pitifully naked thighs, did you regret the minimalist habit. Thigh highs would have been great.

You’re frowning down at your legs when the door opens.

“Thought he’d never go to sleep,” Dean grumbles as he sneaks inside. Then, he looks at you on the bed. “Woah...”

Your heart races at his reaction and you smirk. Thigh highs might have killed him. You slowly push off the bed, taking careful, measured steps to him, licking your lips, and eyeing him up and down. 

He closes the rest of the distance in a flash and then he’s kissing you, his hands roaming your body greedily. He thumbs your nipples through your bra, ghosts his fingers down your side, grabs your ass and pulls you impossibly closer. And you let him. You let him take over your body, let him coax pants and moans out of you, and tell yourself that you’re being generous, instead of selfish as his lips slide down your neck and his teeth graze your skin.

“Dean…” You move your hands to his shoulders, telling yourself you’ll push him away, but your hands don't listen and instead you're clawing into his shirt. You should’ve tied him up. “I’m supposed… to be thanking you…”

He hums against your skin. Then he’s pulled your bra cup down and his warm fingers flick and tweak your nipple to a peak. The sensation is enough to shock you and you buck away from him. For the briefest of moments, he’s not touching you and your head clears. You grab his shoulders, swapping your positions and roughly throw him onto the bed.

You know he let you. He’s too strong for you to overpower him on your own merit and if you weren’t sure, the cocky smirk he has would be proof enough. God, he’s such a brat, you think.

“Take off your pants,” you order, adjusting your bra back the way it was. His eyebrow quirks up at your tone and you feel this unspoken game beginning. “No,” you correct, “ _Strip_.”

He lets out a stuttered breath and you feel heat course through you. He _likes_ this. Fuck. _You_ like this. Dean Winchester, so calm and collected, so self-assured, so… pretty. And here he is, naked on your bed, his cock already stiffening up and you haven’t even touched him. You wonder how hard he could get before you touch him.

You lick your lips. Being on display, you bring up one hand to trail down your body, watching as his eyes obediently follow. “Do you remember what I said earlier?”

He nods. That cocky smirk is still in place and as much as you like it - a fact you will NEVER say aloud- you want to see him desperate.

You walk over to him, keeping some distance as you stand over him. “I need you to behave.” You bat away his hands when he reaches your thighs. “Which means you keep your hands to yourself.”

His smirk is replaced with a frown.

“If you don’t behave, I’ll have to tie you up.”

He shifts on the bed and you delight in how hard he’s getting already. “Fuck,” he grumbles under his breath. “I thought you were a virgin before.”

“I was,” you smile. You slowly get down on your knees, sliding your hands up his bare thighs, purposely avoiding his aching cock. “Doesn’t mean I was a prude.”

He takes a deep breath through his nose while he watches you, each time you make your way up his thighs you get a little closer to his cock. You wrap your fingers around the base and his body stiffens. Just as quickly you release him and rub back down his legs.

His head lolls back while he groans in frustration. “Come on! Is this really you being thankful?”

You can’t help but laugh. He’s right. You shouldn’t really be teasing him this much. As contrition, the next thing he feels is your mouth around his cock. You close your eyes while you take his cock and he moans. You hear his hands lift off the bed and, for a second, feel them touch your hair before he’s clutching the edge of the mattress. 

You whine onto his cock, pulling off with a wet pop. “Good boy.” You stroke his slickened cock, taking the time to lick and suck the head while you toy with him. “I’ve been waiting to do this all night,” you confess, your skin flushing from the admission. “I needed you in my mouth.”

“Fuck…” Dean gasps, thrusting up into your hand.

For some reason, it’s so easy for you to be honest like this. It’s easy now, to tell him how much you wanted him, to openly and unabashedly appreciate him. You take note of all the cute little faces he makes while you work him. How his mouth parts when you lick the head of his cock. How his face contorts in pleasure when you lick a line up his shaft. 

You take as much as you can in your mouth, stroking the base in time with each bob of your head. You feel him get impossibly harder and his breaths get faster. His cock pulses in your mouth and you know he’s close. Then his hands are in your hair, pulling you away.

“What did I say about your hands?” you tease.

Dean shakes his head, demanding breathlessly, “Let me fuck you.”

A rush of heat flows through you, straight to your core. You know you’re wet just from sucking his cock, but your pussy throbs from his suggestion. You feel your dominatrix guise slipping, so you try to get it back. “I want you to cum in my mouth.”

Dean’s hand moves down from your hair to cup your jaw, his thumb brushing over your lips. “And I want to fill that pretty pussy with cum.” He leans down, kissing you, and, without thinking, when he sits back straight, you follow him up, allowing him to guide you. The next thing you know, you’re straddling him. “Don’t you want that, babygirl?” he whispers against your lips.

You whine and only allow yourself to nod.

His nose brushes against yours. “Say it.”

Your pulse pounds in your ears and you take a shaky breath.

His hands glide up and down your back, one coming up to knot in your hair. Ever so slightly, he tugs. “Say “I want you to fill me with cum.””

You bite your lip and when you don’t immediately answer, you feel his hand tug harder and you squeak, “I-!” His hold relents. Your entire body is on fire from shame and exhilaration. “I want you… to… fill me with cum.”

He kisses the side of your mouth, then your jaw, coming to your ear. “That’s my good girl,” he purrs.

You nuzzle his head until your foreheads touch. “You don’t think it’s weird?,” you whisper secretly, as if someone was listening in.

Dean laughs and kisses your forehead. The sweet gesture isn’t something you would have associated with him before and you wonder now why you ever thought that way. Dean was nothing but accepting, albeit in a way you weren’t used to. He wasn’t about to wax poetic about anything -except maybe pie- and there was something uniquely reassuring in that kind of quiet acceptance. He didn’t _have_ to say anything nice because, to him, it wasn’t even a question. That’s why he’d give you a look sometimes like “Why are you even asking?”.

You lean back, carefully holding his face as he squints back at you suspiciously. There’s the “Why on Earth are you asking that?” face and you smile at him. “You’re so cute.”

Bless his heart, he actually looks offended. “I am not _cute_.”

“Yes.” You kiss his nose. “You are.”

He wiggles his nose to get your affection off of him and you attack his face, peppering him with kisses. He gets his hands on your shoulders to hold you back and you glare at the offending appendages.

“Am I gonna have to tie you down?,” you threaten.

“Oh, babygirl….” He lets his hands run down your shoulders, tracing your arms delicately until they’re at yours wrists. “I’d like to see you try.”

He, unsurprisingly, grabs your wrists the moment you try to wrestle free. Straddling his lap means your feet are off the ground, so from there he has an easy time, flipping you onto your back and with your hands next to your head.

“Little thing like you…,” he gloats from above you. “You’re too easy to throw around.”

Maybe he’s just trying to tease you, but he hits on something real inside you and now you’re actually mad. “I didn’t want to hurt you,” you argue.

He scoffs, “As if you could.”

Your pulses races, fear coursing through your veins, turning your blood to ice. You need to get out. You need to get out now. You take a moment to writhe under him, rolling your body to lure him in. Once you feel his grip relax…

“Son of a _BITCH_!”

...you break his nose. Maybe? You actually didn’t get a good look.

He sits back on his knees and sniffs. You can see him blinking back tears, so you definitely hit your mark. 

Oh. Shit. You hit him. You _hit_ him!

“I’m sorry!” you say while laughing. Fuck, stop laughing. Why did your body go with laughing as a reaction? “I’m sorry! I didn’t-! I thought-!” You can’t even finish a sentence because you have no words, so you just sigh. “I am so sorry. Let me look at it.”

He shakes his head and blinks some more. Then, his stare is dead set on you. “Didn’t wanna hurt me, huh?” He smiles for a second before shaking his head again. “Fuck…”

You cover your face with your hands. “This is not what I had planned for the night.”

“Oh, really? Seems like you want to tie me up and beat the shit out of me,” he retorts and you both laugh. 

“I _wanted_ to suck your cock and make you feel nice,” you admit. Great job so far, you think sarcastically. “You… You made me feel nice and…” It’s hard to be honest again. “I wanted to return the favor,” you finish weakly.

“It’s not like that.” Dean laughs through his stuffy nose. You look up through your eyelashes at him. “It’s not a I-did-you-so-you-do-me deal. Sometimes, you just go with the flow.”

“So you didn’t like it?” you fish blatantly. He knows it and just shoots you a look. “What?”

“You know I did. Don’t act dumb.”

Then he’s crawling back over to you and you take a mental snapshot of a naked Dean Winchester crawling to you in your bed.

“You’re not mad at me?” you ask innocently, hoping your doe eyes work on him.

“Do you want me to be mad at you?” he asks.

The loaded question sends a surge through. You lick your lips. “Maybe.”

His hand is in your hair, tugging at the strands, arching your neck to the side, and he sucks hard on the exposed skin. You can feel his tongue swirl as he sucks and bites your flesh, arching into it even when it stings. His teeth scrape down your collar bone and he roughly pulls your bra up to expose your breasts. You moan openly as he gropes your tits and his mouth works his way down.

“That’s my girl,” he whispers before taking your nipple in his mouth. He licks and sucks it to a peak and then tweaks it with his fingers, gauging your every reaction. “So dirty for me.”

You cry out, writhing under him and meaning it. When you move, you feel his cock hardening again. Of course, he lost it when you punched him in the face. “Fuck my mouth,” you plead. “Please. I want you to use my mouth.”

He sits back on his knees and waits there, stroking his cock. “Well?”

Another surge of heat rolls though you and you crawl over to him. His hands go to your head and he guides your mouth to his cock. You try to take as much as you can and it’s easy at first since he’s not completely hard. But, fuck, feeling him grow in your mouth makes you moan and you feel his cock pulse when you do.

“That’s it…,” he pants when you reach your limit. You’re fighting back your gag reflex while he holds you to his cock. “Take it, babygirl.” He moans and guides your head away. “You like taking my cock?”

You can’t answer with your mouth full of cock, so you moan appreciatively.

“You like being my good girl. Letting me use you how I want.”

You’re moaning the moment he calls you his good girl. Yes, yes, yes, you want to say.

“So fucking good…,” he pants. “Your mouth feels so. Fucking. Good.” He thrusts into your mouth as he speaks, gagging you and making you moan. He lets you off his cock and you pant, saliva dripping down your chin.

“Turn around,” he orders.

You’re already on your knees, so you know what he wants. A shiver runs down your spine as you obey. You cry out as he smacks your ass. Then he’s rubbing the reddened flesh and pulling your panties off.

“Sorry, babygirl,” he drawls, sounding anything but, groping and rubbing your ass. “I love your ass.” He gives it another playful smack and you gasp. “Now…”

You feel the bed shift as he scoots forward on his knees, feel his thighs press against yours, and feel his cock slide against your dripping pussy. He grinds into you, the head of his cock rubbing your clit with each thrust.

“Hmm…. fuck…,” he groans and you push back on him. You hear the smirk in his voice. “I could stay like this. Fuck your thighs and cover you in cum. Just. Like. This.”

You whine, jutting back into him, trying to arch your hips in a way that gets his cock inside you, but then his hands are at your hips holding you back while he grinds into you.

“Is there something you want, babygirl?”

“Yes,” you pant.

“Hmm…” You hear him smiling so the slap to your ass is a surprise. “You have to say it.”

“Please, fuck me,” you beg without thinking.

“And?...”

AND?! Your brain scrambles to think of the correct formation of words that will continue this event. Then, you remember. “And fill me with cum,” you add desperately. “Please. _Please_ , fill me with cum.”

His cock slides into inch by inch and you both moan at the sensation. He’s still so much for you, but it doesn’t hurt at all this time. “Fuck, you feel so good,” you pant. And he does. You can feel all of him, every last, raw inch of him inside you. This is so much better than the last time and you didn’t think anything could top the last time.

His cock feels so different this way. He hits so deep inside you that you make unholy sounds. You shove your face into the pillows when you feel a particular loud one brewing and gasp for breath when you can. Dean seems to be making it his mission to get you to forget and scream out wantonly and you’re pretty sure he’s going to get his wish any second now.

His hips piston into you, his hands gripping your hips, guiding you back onto his cock while he mutters curses and praises under his breath. One thing you regret about this position. You miss hearing every sound of his in detail when his head was buried in your neck, you miss each pant and grunt. You miss his face too. You can only imagine how he looks right now, plowing into you with abandon. 

Then his lips are at your spine, your bra undone and tossed away, then he’s moved on to your shoulder, then your neck, and he’s hunched over you, pulling your face to his. Neither of you can keep up the pace while kissing, so you give it up and you let his tongue slip past your teeth. You roll onto your back, wrapping your arms around his shoulders, and pull him down with you, your lips never leaving his. 

Without interruption, his cock slides back into you and he starts a lazy rhythm. You hold him close, rolling your hips into him, wrapping your legs around his waist. You can hear him again. He sounds so good like this, panting into your ear, gasping your name when he takes breaks to breathe. Otherwise, he’s licking into your mouth, sucking your bottom lip, devouring every sound he pulls out of you.

This is so much better, you think blissfully. You didn’t think it could get better, but, fuck, you just melt into each other now. You know how he’s going to move. You know what he likes and something burns deep into your gut at that, that you have something so intimate. And he knows what you like. Everything he learns, he’s weaponized against you, leaving you needy and pleading, and you would be angry if he didn’t give as much back. 

“I love your body… You feel so good,” you pant. He groans into your neck. “Fuck, baby…” His teeth sink into your shoulder and you claw in his back. “Fuck, yes! Yes!”

“Hmm, babygirl,” he growls. 

He slams into you harder now and you urge him on with breathless pleas and “Yes, yes, yes…” You can’t focus on words anymore. You close your eyes and just enjoy him all around you, the smell of him, the taste of him, the sound, and, fuck, the feel of him.

“Dean… Baby, I-” Your voice cuts off with a whine.

He pants a curse into your skin. “Gonna fill you up… Fuck! Gonna… Hmm… Gonna pump this pussy full of fucking cum.”

“Please! Yes! Yes!” Just the thought of it, of his cum dripping out of you, has you hotter than you’ve ever been. You clench around him, a familiar pressure building inside you as he fucks you how he needs. “Please, don’t stop… Please, fuck! Just like this. Just like this.” 

You cum with a gasp and whine, squeezing his cock for all it’s worth. He follows behind not long after. You feel his chest rumble with a laugh and then his lips against your shoulder.

“Fuck,” he sighs happily, pressing his forehead into you. “You feel so good when you cum.”

You take to petting his head, carding your fingers through his short and deceptively soft hair. Plus you like him close like this. You let out an equally happy sigh. “I didn’t think I could. I never came like that before.”

For that, he picks back up on his elbows to smirk down at you. “I’m getting all the firsts, huh?”

“Apparently,” you smirk right back.

He pulls out of you to lay down and this time you don’t hesitate to snuggle up to his side, even with the mess between your thighs. His hand traces up and down your side and wiggle away.

“Stop. I’m ticklish,” you warn with a smile.

“Oh?” he says mischievously.

You glare up at him for a moment before shaking your head and snuggling back into him. “It’s like you want a broken nose.”

“That was a lucky shot.”

“Oh?”

“It was not,” he corrects. “It was skilled and precise.”

“Damn straight,” you say, relaxing your hand against his chest. You venture a glance up. “...Does it hurt?”

He shakes his head. “I’ve had worse.”

You frown at his non-answer. Then you scoot up and gently, as to not put too much pressure, you kiss his nose. “Is that better?”

He gives that quiet and cozy smile. “Much better. Thank you.” 

Something comes to his mind and he gets up and out of bed. You try to school your face to not look so disappointed when he turns around, but when he does, he’s coming back to you with his boxers in hand. He takes the material and swipes up your legs, hastily cleaning up your shared release. You didn’t even know what he was going to do at first. You just opened your legs to make it easier. When did you become that comfortable with him? Next, his boxers are tossed away and he’s back in your bed, situating you next to him like you had been as if nothing had happened.

“Figured we should take care of that now,” he reasons. “Before you fall asleep.”

“Before _I_ fall asleep?” Your outrage is overshadowed by your yawn. “What about you? It’s late.”

“It is,” he agrees, closing his eyes and finally giving into the compulsion to yawn as well. “That’s why we took care of it now. You wouldn’t want to wake up to that.”

We. You want to argue that it was all him, but then you think that you like being part of a ‘We’. And you like how he smells, even when he’s kind of sweaty. And you're pretty sure you say that part out loud because you feel his chest rumble with a laugh, but it’s hard to tell. Your eyes are heavy and your brain is fuzzy. You feel him talk since your head is on his chest, but you’re asleep before you can make out the words.  
  
  
  


**Notes for the Chapter:**

> I had this in mind as soon as I wrote the first Dean chapter. BITCH! If you had asked me if I had such strong opinions on this, I would have said no. Now I KNOW I am a liar. I went off on some deep emotional truths for one Dean Winchester. My husband keeps reminding me that the show is over. BUT THERE WILL BE NO PEACE, FOR I WILL NEVER BE DONE! 
> 
> That's a terrible joke 'cause it's... you know the song? Nevermind.
> 
> On a more sane note, I really love delving into the reader character's insecurities with Dean and just showing (or trying to show) that a lot of it is misconceptions. Like, I don't think Dean would ever describe himself as a kind person, but I think he is one. Is he outwardly kind all the time? Hell no. If we're talking love languages, I think he shows love 100% by acts of service, BUT does not feel comfortable on the receiving end (*cough cough* because our poor boy lowkey-highkey doesn't feel deserving of love and BITCH, I've been there! *cough cough cough*) ... So, yeah, what was I saying about a sane note?
> 
> Dude... I made her hit him in the face. IN. THE. FACE! lmao But it's like... Him overpowering her touched on some real insecurity she had! It's like, "Oh, you think I'm weak and defenseless?" BAM! This is why, when delving into kink, you discuss things beforehand and have safewords. But these two idiots can't speak openly to each other to begin with. Does anyone expect them to be filling out sex surveys and analyzing the results? Please, don't hit your partner in the face (without their consent) ((Also have a safeword))
> 
> Also, Switch!Dean is canon! NO ONE CAN TELL ME OTHERWISEEEEEE! If you ever think you need to choose between being a sub or a dom, I'm here to tell you that you do NOT!


	5. Tail Between Your Legs

**Summary for the Chapter:**

> Reader apologies to Dean after a certain event happened in Chapter 4. Sorry, no smut.
> 
> P.S. What I started as a one shot is CONSUMING MY LIFE. Send help?

Dean’s making eggs for himself. He asked if you wanted any, but you shook your head. Your stomach still felt uneasy, guilt eating away at your appetite. Sam’s on a run while you mope behind Dean, trying to drum the courage to talk.

“I’m sorry,” you blurt out. If you wait too long then Sam will be back and you’ll put off saying it for another day. “About last night.”

Dean glances at you before he’s back to his scrambled eggs.”You still thinking about that?”

“Yes!” you shout, irritated. Of course, you were thinking about it! You two hadn’t talked about it and every time you tried, he brushed you off. “It’s messed up.”

He shrugs and plates his eggs. “It happens.”

“It-! What? Do people hit you?” you ask with sudden, urgent curiosity. His shrug and refusal to look at you is not the answer you wanted. “No one should hit you,” you say sincerely. Your quiet voice feels too loud since there’s no other sound to compete. Dean’s stopped eating. “ _ I _ shouldn’t have hit you. ...I’m sorry.”

“Okay” he says and scoops up a mouthful of egg.

Okay. Okay?!

“Why are you being so difficult?” you gripe.

“I’m not,” he says with his mouth half full.

“I’m trying to talk to you.”

Dean nods, “Yeah. And I’m telling you, you don’t have to.”

“Yes, I do,” you press.

He drops his fork. “Fine,” he sighs. “What do you want to talk about?”

“I…” Suddenly in the hot seat, you’re not sure where to start. You lick your lips and fiddle with the long sleeves of your shirt. “Being a hunter, you get… held up. Sometimes. And… Sometimes, they say... things.”

When you glance up, you see Dean nod along. His attention is too much.

“This is stupid. Eat your breakfast.” You try to abort, but he cuts you off.

“Hey...” He reaches out to touch you, but then hesitates. You look down at your feet in shame. “I didn’t mean to- Look. You can tell me to shut up. Whenever. Okay? You can tell me if you don’t like something.”

You watch him reach out, taking his time, waiting for you to pull your hand away as he takes your hand in his.

“I’d never hurt you,” he promises and gives your hand a little squeeze.

You sniff, your eyes watering, and rub your face off on your sleeve while you squeeze back. “I know.” You let your hands dangle between the two of you and you watch them instead of looking him in the eye. “You can…” You sigh, breaking your hands apart to cross your arms. “You can eat. Your eggs are getting cold.”

“I’m not hungry.”

Now, you meet his eyes to shoot him a look. Really? He’s  _ not _ hungry?

Dean rolls his eyes. “Okay, I am. But I don’t want you to be upset.”

“I’m not upset,” you say, sounding what the layman might classify as “upset”, so now it’s your turn to roll your eyes. “I have a lot- It’s just a lot. Of stuff. It’s not you. I gotta… I don’t know.” You shake your head. “I don’t know.”

“Do you want some eggs?” he asks.

Eggs. That’s his great answer to your existential crisis. “Eggs?” you laugh.

“Yeah, come on.” He gestures to you to follow him and pulls out a chair for you at the table. “You need to eat.” He waits a beat and adds, “I’ll make toast too.”

You don’t want to smile because, for some reason, part of you wants to cling to all the bad feelings you’d been harboring and obsessing over this morning. You know what the bad things feel like. You’re not sure about whatever  _ this _ is that you feel brewing. It feels nice, but it’s so new that you’re not sure how to qualify it.

In an epic display of bravery, you take the seat he offered. “Eggs  _ and _ toast? Didn’t know you were a cook.”

“Oh.” He tosses the spatula in the air so it spins, pointing it at you once he catches it. “I’m top chef.”

“You’re a dork,” you counter, a full smile on your face. 

You  _ know _ he heard you because you catch him smiling before he turns around to the stove. “I wish we weren’t out of bacon,” he laments. “I’ll head to the store later.”

“I’ll come with,” you offer, not even thinking. “If you want…”

You can hear the smile in his voice as he cracks another egg. “Sure.”

  
  


**Notes for the Chapter:**

> Guys. Guys! Are they falling in love?! AM I WRITING AN EPIC LOVE STORY?! THIS WAS SUPPOSED TO BE A 3 CHAPTER MAX THING.
> 
> I need to honestly just separate the Sam chapter at this point!
> 
> WHAT AM I DOING WITH MY LIFE?!
> 
> Also my sister is impressed that I keep having titles with "tail" in it. (I am too.)


	6. Details... Details...

**Summary for the Chapter:**

> A further continuation of the Dean timeline because apparently, in my heart, that is the true timeline and I have a lot to say about it.
> 
> Sam and Dean take the reader to get an anti-possession tattoo. And yes... there IS smut. >:D

You closed the Dragon case a few days ago and you told herself when you hitched onto the Winchester Wagon that you would leave when it was over. That made sense back then. That was before they took you to the Bat Cave. Whoever the Men of Letters were, they knew their shit and this bunker had everything. Including hot water.

You think of your old apartment in Iowa. It wasn’t the worst place you had ever lived in, but it wasn’t the Ritz either. Scrounging up enough to make rent meant sometimes other bills got put off. So you figured out how to work with bare essentials, never asked for anything, and you managed. You got by.

Neither brother had brought up you leaving yet. In an effort to keep that the case, you scoured through reports to find something to make yourself useful. You, Sam, and Dean end up in the study together most nights, all huddled close at one end of the long table, and tonight is no different.

Sam brings you a cup of coffee and your quick “Thanks” drawls out into a yawn. You let yourself have a nice, long stretch in your chair, hearing Dean walk up as well. Your shirt ends up bunching a bit when you lean back onto your chair, leaving your lower back exposed, and you pull it down. You open your eyes, noting that Dean’s footsteps have stopped behind you, and turn around.

“You don’t have any tattoos,” Dean says thoughtfully.

Sam looks up first at his brother, sharing some kind of silent message, and then he’s looking at you and you fight back the urge to shrink under their combined, suddenly intense gaze.

“You need one,” Sam insists.

Sam’s worry unsettles you more. “Uh… I guess? I never could think of one I wanted, so…” You shrug, hoping that’s that.

Dean shakes his head. “You need _this_ -” He pulls down the collar of his shirt enough to expose the tattoo on his chest. He’s going to stretch out the fabric, your brain cries unhelpfully. “Anti-Possession symbol,” he says.

When Dean lets go of the fabric, it is indeed stretched out, and inwardly you lament over his carelessness. You liked that shirt on him. “Possession? You guys worried about demons that much?” you joke.

They both get a somber look and you don’t need the backstory to know it was something big. 

“I’m... sorry for your loss.” _What_ loss doesn’t matter. You know that. Loss is loss.

Dean breaks the heavy silence first, “Consider it a new industry standard.”

“There’s a place nearby. They should still be open,” Sam adds and your head swivels to the younger Winchester. Before you can say anything though, Sam’s on the phone. “Hi. I was wondering if you had anyone available for a quick piece. Simple, one color, about 3 inches by 3 inches...”

“Wow! So… tonight. We’re doing that tonight,” you say to Dean.

“Sooner, the better,” he replies, taking a seat next to you, leaving his usual spot across the way empty. “Start thinking of where you want it.”

“They have a guy, but we gotta head out. They want to close on time,” Sam says with an accomplished smile.

“Great.” You hear a teeny, tiny hint of a smile in Dean’s voice. 

“Great,” you repeat dryly. 

You wish you could be as enthusiastic about this as they are, but everything is so sudden. You’re still not sure where you want it. The boys talk-slash-argue about something on the drive. You catch Dean saying “I almost got tetanus from that place.” but you’re too distracted to listen in.

Maybe your arm? That won’t hurt too bad. Lots of people get tattoos on their arms. You pull your jacket down and shirt sleeve up to see the bare skin and flex your bicep. Yeah… But the symbol only works if it’s _on_ you. Imagine getting your arm sliced off AND getting possessed by a demon. That’s gotta be the world’s worst 2-for-1.

You tug (delicately) at the collar of your shirt. You could get it where the boys have theirs, but it’s going to be on top of your left boob. It’ll look weird, you think with a pout. It looks nice on them, but you think it will make your chest all unsymmetrical. So then, symmetry. You can get it lower, on your sternum, under your breasts. You pull your shirt away to look at your chest, imagining the tattoo where your bra sits. Hmm… That could work.

“Enjoying the view?” Deans asks with a smirk.

Sam chuckles, getting out of the car and letting you out of the back.

Here already. Damn. “Did you speed all the way here?,” you quip.

“They were gonna close!” Dean says in defense.

* * *

After a quick discussion and quick mooning on the part of your tattoo artist - _“You get it? Demons can kiss my ass!”_ \- you were in the chair and, apart from flashing you his ass, the artist, Darryl, was very professional. He’s got your shirt taped down around your breasts, so you’re not topless in the shop. Your bra, you have tucked next to you in the seat and he warns you that you won’t wanna wear one for a bit after. Turns out, he didn’t realize from the phone call that any of you were hunters and is absolutely tickled to have you in his shop. The conversation helps pass the time, but nothing can distract from the needles stabbing into your ribcage.

You grit your teeth. You think about breathing like you’ve seen pregnant ladies do on T.V., lamaze or whatever, but you also are afraid to breathe, lest Darryl’s hand slip and you end up with a mangled chest and flubbed symbol.

The tattoo gun lifts off your chest and Darryl dips the gun in more ink. “You gotta breathe for me, okay?”

You nod your head.

“You holding up?” Darryl asks, his wrist anchored against your ribs and you close your eyes to brace yourself.

Just as you nod, you feel a hand tap the claw you have digging into the armrest. You open your eyes, just as the needle hits, and wince up at Dean. “You asking… me.... to hold your hand… Winchester?”

Deans smiles down at you. “Yeah,” he says dryly.

You take his hand, wincing each time the needle goes over the center of your ribs. You squeeze Dean’s hand particularly hard and then you feel him bring his other hand over yours, his thumb rubbing up and down.

“I should’ve... got it... on my ass,” you say, earning a laugh from all the guys.

* * *

The next day sucks. Darryl didn’t need to tell you to not wear a bra. You cannot imagine anything touching or rubbing the center of your chest right now. Your tits are bad enough! You never realize how much your chest moves until you have a big ass wound smack dab in the middle of it. Your loose shirt is comfy as you can get without straight-up going topless, so you deal.

“I can’t believe I paid for this experience,” you gripe at breakfast. That was another thing that was different from Iowa. You had someone to gripe with at breakfast.

Dean scoffs, but you can tell he’s smiling as he cooks. “Don’t be a baby. It’s not that bad.”

“You don’t have boobs! I can’t control these things. They’re on the loose!”

Sam chokes on his shake and recovers with a cough. “Yeah, they’re America’s Most Wanted.”

“Damn straight they are.” You point to your left and right breast, ignoring how it pulls the healing skin. “Good ol’ Thelma and Louise.”

“No wonder you were a virgin,” Dean retorts.

“Hey!” you cry in mock annoyance and throw a piece of your cereal at him, laughing. “Don’t be mean.”

“I’m going for a run,” Sam says with a shake of his head. “Don’t kill each other while I’m gone.”

Then the kitchen is quiet. You eat your cereal while Dean finishes up his egg sandwich, the sizzle of the griddle the loudest thing in the room. You’ll both be done eating soon. You do not like moments like this. Moments like this will inevitably lead to the “When are you going back home?” conversation and so far, neither Sam nor Dean had asked that question. So you needed to make sure, you steered away from that.

“So, have you thought about-”

“When did you get your tattoo?” you interrupt.

Thank God, it’s Dean and not Sam. Dean isn’t big on talking as it is, so your guidance is more easily accepted.

“A few years back,” he answers.

“Sam too?”

“Yeah.”

“Cool,” you say dumbly. You could push for more information on _why_ they got the tattoos, but, from the looks you got last night, that wasn’t going to be a light-hearted conversation nor was it a breakfast conversation or a conversation you ever needed to have, honestly.

A thought strikes you. “Why didn’t we go earlier? I mean… You’ve seen me naked. You knew I had no tattoos.”

Dean’s eyes drag down your chest and he licks his lips and in just a shirt there’s no hiding how your nipples harden. “I hadn’t seen all of you.”

You snort and cross your arms loosely around yourself. “How much more do you want to see?”

He stands up and you act unaffected as he nears just as you act unaffected when he only clears your empty bowl, taking the bowl and his plate to the sink. He turns around and leans on the counter. “How are you feeling?”

Feeling? Is he asking if you’re sick? Or…?

His eyes flicker down to your chest and then back up.

Oh. 

“I’m alright,” you assure.

Dean smirks and closes the distance. “You sure?” He takes your hand and guides you off the stool to stand with him. “Don’t need you clocking me again,” he jokes.

Your face crumples. “I said I was sorry,” you whine. “I meant it. I-”

His lips interrupt your sentence and thought. One hand trails up your side, giving you goosebumps and a shiver, before he kneads your breast through your shirt. His touch is gentle and exploratory and you arch into it. He breaks away from your mouth to kiss up to your ear.

“I want to see all of you,” he confesses. “But you’re so shy…”

“I’m not-!” He tweaks your nipple and you squeak. “Shy.”

“Look at you trying to hold back.” He looks down at you as he rolls your nipple between his fingers, watching you squirm. “You don’t need to, babygirl. I’ll bet you sound so pretty when you scream.”

You look back to the doorway, craning your neck behind you. “S-Sam-”

Dean tsks, kissing your neck before giving you a playful bite. “Wrong name.”

You bite your lip. “Sam will be back,” you correct with a roll of your eyes.

“So we should make this quick,” he says. Then he’s got your pants pulled down and he’s lifting you up onto the kitchen island.

“Dean! People eat here! _We_ eat here!”

“We do,” he agrees. 

Then, he’s tugging your pants all the way off and bending down. His tongue sweeps up your pussy and you buck. His mouth returns, softer, slower, working you into a frenzy so agonizingly slowly. You know he could do more because he’s _done_ more. Now he’s just teasing you and just as you really start getting into it he stops.

The brief pause gives you enough sense to remember where you are: the middle of the wide open kitchen. You open your mouth to speak as he rubs his cock against your soaked pussy and let out nothing more than a needy cry. You bite your lip when he slides his cock in.

“We…” You swallow. “We need to stop,” you say, even as your arms wrap around him, pulling him closer.

“Oh?” He works his cock into you at a slow pace. “But you sound like you need it, babygirl.”

You clench around him, dig your nails into his shoulders. “Faster.”

“Faster?” he teases. His hips keep up their slow, steady pace. “I thought we should stop.”

“Dean,” you groan. Your chest rises and falls with each pant and you feel your tattoo ache. “You’re such a jerk.”

He laughs and mercifully quickens the pace. His lips find their way back to you, gliding down the column of your neck, leaving your mouth free to expel every curse and pant he works out of you and the praise he showers you with only elicits more.

“That’s right, babygirl. Fuck, I want you to scream.”

“I-” You helplessly take his cock as he holds your legs around his hips, but even so, the cold (but steadily heating up) metal of the island reminds you where you are. “I can’t. Dean.”

“Shh… Yes, you can. It’s just me. Just me here, baby.”

You close your eyes and let out a long moan. The sound practically echoes.

“So fucking good. You sound so pretty like this. That’s right. Let me hear you.”

Your moans intertwine with his and fuck, he sounds heavenly like this. You stop thinking and just let go, words tumbling from your lips spliced with breathy moans and long whines, all accompanied by the wet pounding of his cock into your pussy. He feels so good when he cums that you don’t even think twice, you do as he said and you scream, surprising even yourself with the volume. Self-consciously, you slap your hand over your mouth.

Dean’s laugh now rings out and it’s the loudest, happiest sound you’ve heard out of him. “I didn’t think you’d do it.”

You slap his chest and pout. “You _told_ me to!” You can feel your face is on fire.

“I still didn’t think you would.” He kisses your cheek when you refuse to look at him. “It was hot.”

You turn only your eyes to keep up your cold shoulder. “It was?”

Dean pinches your chin to get you to face him and then presses his lips to yours. “It was.”

After he pulls away, he grabs some paper towels and hands some to you. Jesus, you’re never going to be able to eat breakfast here again. You pull your pants back on and a thought strikes you.

“You didn’t get to see much of me,” you say, shaking your big, billowy shirt as evidence.

His eyes pin you in place and it doesn’t matter that you’re fully dressed because you feel naked, _exposed_. “I see more of you each time,” he says.

**Notes for the Chapter:**

> I had to write this because after writing multiple chapters of smut and not mentioning the reader having a tattoo, suddenly bringing up a tattoo felt dishonest (because I'm a crazy person). See other people have FUN writing whereas I'm up at 3am googling laws and weather patterns in Tennessee. YES, THAT IS TRUE AND, NO, I WILL NOT TAKE QUESTIONS.
> 
> I have a LOT more in store that I'm currently outlining. It will definitely be one arc over multiple chapters. My question to all of y'all, is do I just start a new work?? This has gotten away from me. This was supposed to be 3 chapters: one setup, one Sam, one Dean. And now I'm outlining what is basically an entire episode of Supernatural, complete with murder, mystery, and b-plots, and I wonder how I got here...
> 
> If I do make a new work (which I'm heavily leaning towards) I'll make it the second in this "series". So be on the lookout for that! <3

**Author's Note:**

> I am going for Alternate Timelines with this. So we get you with Sam AND you with Dean. You're welcome. (Because I legit couldn't choose which one to write about.) 
> 
> I wrote this at 5am in the year 2020!! IN THE YEAR 2020, I AM STILL WRITING SUPERNATURAL SMUT?!?! I'd say I'm disappointed in me, but I am shameless and I love this story.


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